July 16, 2026

Career Pivots Are Messier Than They Look

Career Pivots Are Messier Than They Look
Loud & Lifted
Career Pivots Are Messier Than They Look

Career pivots sound exciting until you are actually living through one.

The uncertainty. The second-guessing. The loss of routine or identity. The pressure to quickly prove that you made the right decision.

In this Quick Lift, Betsy shares the biggest takeaways from her conversation with Trish Barber, author of Why Women Pivot, along with practical action steps for anyone navigating a career change, reinvention, or unexpected new chapter.

This episode is a reminder that feeling unsure does not mean you are failing—and that you do not have to have the entire path figured out before taking your next step.

Listen: to the full Loud & Lifted episode with Trish for the complete conversation.

Purchase: Why Women Pivot

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Career pivots always sound better after they

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work out. You hear the story after someone left

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the job, started the business, changed industries,

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or finally went after the thing they've been

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thinking about for years. But then it sounds

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confident and intentional, like they knew exactly

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what they were doing the whole time. But when

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you're actually in the middle of it, it usually

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does not feel that clear. It feels messy. It

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feels uncertain. Sometimes it feels exciting,

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and sometimes it makes you question every decision

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you've ever made. I know because I have lived

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it and actually I'm still living it. When I left

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my CEO role, I knew I was ready for something

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different. I was excited about building my own

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business, speaking more, coaching women and helping

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companies in a different way. But that did not

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mean I had every piece figured out. I did not

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leave with a perfect five -year plan, a guaranteed

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pipeline of clients and total confidence every

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single day. There were days when I thought this

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is exactly what I'm supposed to be doing. And

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there were days when I thought maybe I should

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just go get another corporate job. I still think

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that sometimes. And this is the part we don't

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talk enough about. In my conversation with Trish

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Barber, author of Women Who Pivot, we talked

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about what a career pivot really looks like for

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women, whether the change is your choice or something

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that was forced on you. It's not one brave decision,

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and then suddenly everything falls into place.

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It's a process. You are learning, adjusting,

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talking to people, trying new things, and sometimes

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changing your mind along the way. So if you're

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thinking about making a change or you're already

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in the middle of one, here are a few things I

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want you to take away from this conversation.

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Let's get into it. The first is to pay attention

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to what is draining you. Now, not every bad week

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means you need to quit your job. We all have

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hard seasons. We have demanding projects or frustrating

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coworkers, difficult bosses, and times when work

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and life are both asking just way too much from

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us. But there is a difference between a rough

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season and a situation that no longer is right

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for you. Maybe you're no longer learning. Maybe

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your health is affected. Maybe you are missing

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too much of your life. Maybe you keep waiting

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for an opportunity that is clearly not coming.

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Or maybe you just know deep down that you are

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no longer supposed to be there. Usually we know

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before we're really ready to admit it. So here's

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something simple you can do. For the next two

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weeks, pay attention to your energy. At the end

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of the day, write down what energized you and

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what drained you. Don't make it complicated.

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Just look for patterns. Because sometimes the

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question is not, do I hate my job? The better

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question is, is this still the right fit for

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the person I'm becoming? The second thing is

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to separate your identity from your title. This

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one was hard for me. When you spend years building

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a career, earning promotions, and becoming known

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for a certain role, it's easy to start believing

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that title is the value. When I left a visible

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CEO role, I definitely had moments of wondering

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who I was without the company and without the

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title attached to my name. Would people still

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take my calls? Would they still see me in the

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same way? Was all of my credibility tied to that

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position? But your title is not the full story.

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Your experience is still yours. Your judgment

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is still yours. Relationships, leadership ability,

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instincts, and problem -solving skills do not

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disappear because the business card changes.

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So instead of focusing only on the title you

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had, think about what people actually rely on

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you for. What do people always ask your help

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with? What do you do well that may feel natural

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to you but is incredibly valuable to someone

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else? What compliments have you heard throughout

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your entire career? Maybe you make complicated

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things simple. Maybe you organize chaos or build

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trust quickly. Maybe you see the strategy before

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everyone else does. This is the value you carry

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into whatever comes next. The third takeaway

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is to stop treating your pivot like a final exam

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where you are supposed to know every answer before

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you begin. This is where I had to learn some

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patience, which is not exactly my favorite thing.

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I wanted to decide what I was doing and then

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immediately have the business model, the clients,

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the messaging, and the revenue all lined up.

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And guess what? That's not how it worked. There

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was trial and error. Some things gained traction.

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Some things did not. Some ideas sounded great,

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but they actually were not a fit. Other opportunities

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showed up that I had not expected or planned

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for. That does not mean the pivot is failing.

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It means you were learning. Trish talked about

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this like customer discovery. You have to understand

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what people need, what problems they are trying

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to solve, and where your experience can actually

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help. So get out of your own head and go talk

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to people. Talk to someone who works in the industry

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you're considering. Talk to someone who's already

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made a similar move. Or maybe someone who knows

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your strengths well. And do not just ask, do

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you think I should quit? Ask better questions.

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What problems are companies in this space trying

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to solve? What skills are most valuable? What

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do people misunderstand about this kind of work?

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And where do you see my experience transferring?

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You are not asking them to make the decision

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for you. You are gathering information so you

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can make a better decision for yourself. The

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fourth takeaway is to own your story before other

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people write it for you. This matters whether

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you chose to leave or whether the decision was

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made for you. If you were laid off, reorganized

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out of a role or pushed into a change you didn't

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want, you're allowed to feel hurt, frustrated

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or angry. This is real. But when you start talking

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about what comes next, You need a story that

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is confident and forward -looking. Trish made

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a great point in our conversation. Your pivot

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story should not sound wounded. This does not

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mean you have to pretend everything is perfect.

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It means you do not have to lead with the most

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painful part. Instead of saying, I lost my job,

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but I have no idea what I'm doing, you could

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say, after several years in marketing, I'm exploring

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opportunities where I can use my experience in

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community engagement, partnerships, and relationship

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building. Same person. Same situation, completely

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different energy. Your story should answer two

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things. What experiences are you bringing with

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you and what are you moving toward? And that

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story can evolve. Mine definitely has. But you

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need language that helps people understand where

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you're going and how they may be able to help.

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The last takeaway is one of my favorites from

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the episode. Build a personal advisory board.

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I usually call this your circle, but I love Trish's

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language because it makes it feel even more intentional.

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You should not try to navigate a major career

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change alone, and you do not need one perfect

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mentor who can give you all the answers. You

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need different people for different reasons.

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You need someone who will tell you the truth,

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even when it's what you don't want to hear. You

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need someone who reminds you what you are capable

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of, even when your confidence takes a hit. And

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you need someone who can connect you to people

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or opportunities you may not know about. You

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also need people with different perspectives,

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different ages, industries, and experiences.

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The person who gives you the best advice may

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not even have more experience than you. They

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may simply have different experience. So think

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about three people. Who will challenge you? Who

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will encourage you? Who will expand your thinking

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or your network? Then reach out. And be specific.

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Do not send the vague, I would love to pick your

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brain message. Tell them what you're considering

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and why you would value their perspective. People

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are often willing to help, but they need to know

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what you actually need. Here's the bottom line.

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You do not have to know exactly how your pivot

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will end before you begin. You need enough of

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clarity to take the next step. Pay attention

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to what's draining you. Get clear on the value

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you bring beyond your title. Talk to people.

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Own your story and build the circle that will

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help you move forward. A pivot does not have

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to be perfectly planned or every right move,

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but you cannot just leave something behind and

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hope the next thing figures itself out. You have

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to actively build what comes next. If you have

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not listened to Trisha's full episode, I strongly

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encourage you to do so. And until next time,

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stay loud and stay lifted.

Trish Barber Profile Photo

Founder, 3WaysDigital, Author

Trish Barber is a three-time tech-media entrepreneur, CEO of 3WaysDigital (an innovation advisory firm), board member, speaker, and author of “Why Women Pivot”. Her best-selling book reflects her sometimes-successful experience navigating ambition and family while providing a perspective that women find affirming and relatable. She becomes President of Women in Technology on July 1st and is therefore devoted to providing professional development and safe spaces for women from the classroom to the boardroom.